Palladium-Catalyzed Oxidative Coupling between Arenesulfinic Acid Salts and Allylic AlcoholsA Strate

来源 :第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛 | 被引量 : 0次 | 上传用户:arlunfly
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β-Aryl carbonyl compounds have drawn much attention owing to the prevalence of this fundamental building blocks in pharmaceuticals and biologically active natural products.1 Due to their importance,various methods have been developed to construct the β-aryl carbonyl frameworks,such as the redox isomerization of allylic alcohols with transmetal-catalysts,Pd-catalyzed oxidative coupling of allyl alcohols with arenes(Scheme 1,eq.1,2).However,most of these oxidations suffer from relatively high catalyst loadings,high oxygen pressures,an excess of ligand or base.Besides,the arenesulfinite salts have a great potential to serve as ideal aryl sources for C-C bond formation via extrusion of SO2 since they are cheap,stable,easy to handle,and easily prepared from their corresponding sulfonyl chlorides.2 Herein,we report a Pd-catalyzed desulfitative synthesis of β-aryl ketones and aldehydes from sodium aryl sulfinate and allylic alcohols(Scheme 1,eq.3).To the best of our knowledge,it is the first example to realize the highly regioselective Heck-type reaction of allylic alcohols using sodium aryl sulfinates as aryl sources for the construction of β-aryl ketones and aldehydes.
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